Formamide → 3H,4H-thieno[3,2-d]pyrimidin-4-one

HRID 2297751Notes

Reaction equation

HRID 2297751 reaction equation
C[O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH:10][CH:11]=O)=O.C([O-])=O.[NH4+].C([NH2:19])=O>>[N:10]1[C:9]2[CH:8]=[CH:7][S:6][C:5]=2[C:3](=[O:2])[NH:19][CH:11]=1

Participants

4

Reactant 3

HCID 713FormamideHCID 2723923Ammonium formateHCID 2777636Methyl 3-(formylamino)-2-thiophenecarboxylate

Product 1

HCID 1354174223H,4H-thieno[3,2-d]pyrimidin-4-oneYield 72%

Conditions

Temperature
140 °C

Procedure

In a 125 mL round-bottomed flask 3-formylamino-thiophene-2-carboxylic acid methyl ester (5 g, 27.0 mmol), ammonium formate (5.11 9, 81.0 mmol), and formamide (6.40 mL, 162 mmol) were combined and heated at 140° C. After 10 hours the reaction mixture was cooled to room temperature and filtered. The crystalline solid was washed with water and dried in vacuo to afford 2.96 g (72%) of 3H-thieno[3,2-d]pyrimidin-4-one. 1H NMR (400 MHz, DMSO) d 8.10 (m, 2H), 7.34 (m, 1H). LC-MS: 153 (MH′); HPLC RT: 1.21 minutes.

Workup

  1. temperatureAfter 10 hours the reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. washThe crystalline solid was washed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-cbf564e3449c47d1a0fcd19213eff830
Source dataset
uspto-grants-2002_12
Patent number
US06492383B1

Reaction notes

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